CHEBI:59560 - sapropterin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways
ChEBI Name sapropterin
Definition A tetrahydropterin that is 2-amino-5,6,7,8-tetrahydropteridin-4(3H)-one in which a hydrogen at position 6 is substituted by a 1,2-dihydroxypropyl group (6R,1'R,2'S-enantiomer).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Secondary ChEBI IDs CHEBI:64242
Supplier Information
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C9H15N5O3
Net Charge 0
Average Mass 241.24710
InChI InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
SMILES [H][C@@]1(CNc2nc(N)[nH]c(=O)c2N1)[C@@H](O)[C@H](C)O
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 5,6,7,8-tetrahydrobiopterin )
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via 5,6,7,8-tetrahydrobiopterin )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
(via 5,6,7,8-tetrahydrobiopterin )
Application(s): diagnostic agent
A substance administered to aid diagnosis of a disease.
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via 5,6,7,8-tetrahydrobiopterin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sapropterin (CHEBI:59560) has role coenzyme (CHEBI:23354)
sapropterin (CHEBI:59560) has role diagnostic agent (CHEBI:33295)
sapropterin (CHEBI:59560) has role human metabolite (CHEBI:77746)
sapropterin (CHEBI:59560) is a 5,6,7,8-tetrahydrobiopterin (CHEBI:15372)
Incoming sapropterin dihydrochloride (CHEBI:32120) has part sapropterin (CHEBI:59560)
INNs Sources
sapropterin ChemIDplus
sapropterina ChemIDplus
sapropterinum ChemIDplus
Synonyms Sources
(−)-(6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone ChemIDplus
(6R)-L-erythro-tetrahydrobiopterin ChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone KEGG COMPOUND
5,6,7,8-Tetrahydrobiopterin KEGG COMPOUND
6R-5,6,7,8-tetrahydrobiopterin ChemIDplus
6R-L-5,6,7,8-tetrahydrobiopterin ChemIDplus
L-erythro-tetrahydrobiopterin UniProt
tetrahydrobiopterin DrugBank
Database Links Databases
C00018229 KNApSAcK
CPD-14053 MetaCyc
DB00360 DrugBank
EP191335 Patent
H4B PDBeChem
Sapropterin Wikipedia
US4713454 Patent
View more database links
Registry Numbers Types Sources
17528-72-2 CAS Registry Number KEGG COMPOUND
27070-47-9 CAS Registry Number ChemIDplus
4699705 Beilstein Registry Number Beilstein
4699705 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10333495 PubMed citation SUBMITTER
1297822 PubMed citation CiteXplore
16510994 PubMed citation SUBMITTER
19627172 PubMed citation CiteXplore
21466737 PubMed citation CiteXplore
21646032 PubMed citation CiteXplore
22110560 PubMed citation CiteXplore
22112818 PubMed citation CiteXplore
22310224 PubMed citation CiteXplore
22388642 PubMed citation CiteXplore
22391997 PubMed citation CiteXplore
22575621 PubMed citation CiteXplore
22832064 PubMed citation CiteXplore
23235653 PubMed citation CiteXplore
23266371 PubMed citation CiteXplore
23430527 PubMed citation CiteXplore
23430545 PubMed citation CiteXplore
23436109 PubMed citation CiteXplore
23462988 PubMed citation CiteXplore
23690520 PubMed citation CiteXplore
23705856 PubMed citation CiteXplore
23712020 PubMed citation CiteXplore
23743404 PubMed citation CiteXplore
4004257 PubMed citation CiteXplore
Last Modified
23 October 2015
General Comment
2011-03-17 The active enantiomer of tetrahydrobiopterin, sapropterin is a natural co-factor of the three aromatic amino acid hydroxylase enzymes responsible for the conversion of phenylalanine to tyrosine, tyrosine to L-dopa, and tryptophan to 5-hydroxytryptophan. These conversions are particularly important in the biosynthesis of the neurotransmitters serotonin, melatonin, dopamine, noradrenaline and adrenaline. Sapropterin is also an essential cofactor in the biosynthesis of nitric oxide. It is used as its dihydrochloride for the diagnosis and treatment of variant forms of phenylketonuria (hyperphenylalaninaemia) associated with tetrahydrobiopterin deficiency.